Sodium Bicarbonate → 1,3-Dihydroxypropan-2-yl 4-methylbenzenesulfonate

HRID 1601388Notes

Reaction equation

HRID 1601388 reaction equation
C1([C@H]2O[C@@H:11]([O:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:10]CO2)C=CC=CC=1.Cl.[O:25]1CCOC[CH2:26]1.C([O-])(O)=[O:32].[Na+]>CO>[C:20]1([CH3:23])[CH:19]=[CH:18][C:17]([S:14]([O:13][CH:11]([CH2:10][OH:32])[CH2:26][OH:25])(=[O:15])=[O:16])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 86583790cis-2-Phenyl-4-(p-toluenesulfonyloxy)-1,3-dioxane

Product 1

HCID 103772501,3-Dihydroxypropan-2-yl 4-methylbenzenesulfonateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 50 ml of methanol were dissolved 5.00 g of cis-2-phenyl-4-(p-toluenesulfonyloxy)-1,3-dioxane, and 5 ml of a 4N HCl-dioxane solution were added to the solution, followed by stirring of the resulting mixture at room temperature for 2 hours. To the reaction mixture were added 3.5 g of, NaHCO3 powder, and the mixture was stirred for 10 minutes. Then, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The thus obtained oil was subjected to column chromatography using silica gel and eluted with ethyl acetate to obtain 3.70 g (yield: 100%) of the title compound as an oil.

Workup

  1. additionwere added to the solution
  2. stirringthe mixture was stirred for 10 minutes
  3. filtrationThen, the reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-38f92b9cdb864f50a90a7277a05b3dd9
Source dataset
uspto-grants-1999_11
Patent number
US05977152

Reaction notes

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